KEY WEST
Ranked by traveller popularity
The 10 most popular evening experiences in Key West. Here's what they actually deliver, who runs them, and what they cost.
A 2-hour Key West sunset sail on a roomy catamaran with an open bar, sangria, hors d’oeuvres, and live local music.
“Super fun. Great crew and snacks. The musician played a little too much rap and no islandy music, but that being said still a great time!”
Key West sunset dinner cruise with tropical buffet, live steel drum and DJ, and unlimited drinks. 2 hours on a 65-ft yacht.
“Beautiful and memorable experience that you can cherish whole life. We traveled on Christmas eve and it made a perfect celebration for an occasion”
Half-day sailing, kayaking, and snorkeling off Key West, with wetsuits, reef wildlife, drinks and sunset options.
“Wonderful variety of water sports to do. Micah, Anthony, and Laura were very knowledgeable about the wildlife that was seen during our trip. Would definitely recommend to anyone who is up to being on the water!”
Small-group Key West sunset sail with a wine tasting, unlimited beer, and hors d’oeuvres, plus crew stories and a smoother pace for two hours.
“A little late in posting as our sailing was back in December. This was the best sailing ever. Molly and team were stupendous. The level of detail was beyond what we had expected. Plenty of d'oeuvres and wine/bubblies to go around. Crowd was small and provided an intimidate setting for a great late afternoon outing.…”
Adults-only Key West sunset champagne cruise on a 14-passenger catamaran: unlimited wine, gourmet cheese, and Moët upgrades.
“It’s intimate and wonderful. We have done it two years in a row and will come back. It’s a small crew and the food and wine are amazing.”
A 2-hour Key West sunset catamaran with live music, unlimited drinks, and appetizers. Three decks for views. Check in early for seats.
“Great time well organized fun way to see sunset… good music with Killer Dudes excellent service very fun”
Small-group 90-minute sunset sail from Key West with drinks included, a great harbor view, and a water-side look at Sunset Celebration.
“After days with chilly wind, we were able to book an evening sunset cruise for our last evening in Key West. Eric and Carlo took great care of all passengers. They were friendly, informative, and focused on safety for all. The 90 minutes on the water at sunset was peaceful and beautiful. As Jimmy Buffett…”
Key West sunset on America 2.0: beer, wine, champagne, and plated hors d’oeuvres as you pass Fort Zachary and Mallory Square.
“Great foods and lots of it. Tremendous staff, we are all very helpful and courteous. Great time and beautiful sunset. True sailing experience.”
Small-group Key West sunset catamaran with dolphin spotting, premium wine, and chef’s tapas. About 2.5 hours, $89.
“The host and hostess were phenomenal..the scenery with the sunset was worthwhile moment to say the least. I would do it again.”
Key West champagne sunset catamaran with beer, wine, champagne, sangria and light bites. 1.5 hours of captain-led views.
“Great experience. Got sea sick but a god cruise! Expect a lot of people drinking and taking in the views. Just very light apps. A musician as well.”
